3-Chloropropyl(diethyl)amine → HCID 22768838, compound

HRID 1764659Notes

Reaction equation

HRID 1764659 reaction equation
[Na].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][C:13]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH2:27]([N:29]([CH2:34][CH3:35])[CH2:30][CH2:31][CH2:32]Cl)[CH3:28].C[O-].[Na+]>C1(C)C=CC=CC=1.CO>[CH2:27]([N:29]([CH2:34][CH3:35])[CH2:30][CH2:31][CH2:32][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([C:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][C:13]=2[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)(=[O:11])=[O:10])=[CH:7][CH:8]=1)[CH3:28]

Participants

7

Reactant 4

HCID 669183-Chloropropyl(diethyl)amine2×HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 22768860HCID 22768860, compound

Product 1

HCID 22768838HCID 22768838, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1140TolueneSolvent

Procedure

A solution of 0.14 g. (0.006 g.-atom) of sodium in 20 ml. of methanol was added to a solution of 1.1 g. (0.003 mol.) of 3-(4-hydroxyphenylsulfonyl)-2-phenylbenzofuran in 25 ml. of dry methanol and the mixture was refluxed for 0.5 hour. The solvent was evaporated and 25 ml. of toluene and 3 ml. of dimethylformamide were added to the residue. A solution of 0.86 g. (0.006 mol.) of 3-diethylaminopropyl chloride in 10 ml. of toluene was added dropwise and the mixture was refluxed for 2.5 hours. An additional 0.162 g. (0.003 mol.) of sodium methoxide and 0.43 g. (0.003 mol.) of 3-diethylaminopropyl chloride were added and the mixture was refluxed for ca. 16 hours. The mixture was filtered, water and methylene chloride were added and the layers were separated. The aqueous phase was extracted with methylene chloride and the organic phase was extracted with water and saturated sodium chloride solution. The organic layers were combined, dried (MgSO4) and evaporated to dryness to give the title compound.

Workup

  1. customThe solvent was evaporated
  2. additionof dimethylformamide were added to the residue
  3. temperaturethe mixture was refluxed for 2.5 hours
  4. temperaturethe mixture was refluxed for ca. 16 hours
  5. filtrationThe mixture was filtered
  6. additionwater and methylene chloride were added
  7. customthe layers were separated
  8. extractionThe aqueous phase was extracted with methylene chloride
  9. extractionthe organic phase was extracted with water and saturated sodium chloride solution
  10. dry with materialdried (MgSO4)
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-c67f757a066b4f80a4746bf9d0d27442
Source dataset
uspto-grants-1978_09
Patent number
US04117128

Reaction notes

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